Hydrochloric Acid → HCID 60035418, compound

Participants

Reaction Steps

To a suspension of lithium borohydride (11.6 g) in tetrahydrofuran (50 mL) was added a solution of 4-amino-1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (33.7 g) in tetrahydrofuran (100 mL) was added. The mixture was stirred at reflux for 1 hour. After cooling with ice-cooling bath, a 6M HCl aqueous solution was added slowly. The solution was made to alkaline (pH=9) with 4 M NaOH aqueous solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=3:1) to give 1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine (17.9 g) as a solid.

Provenance & Evidence